A few years later, his family moved upriver to
Beverwyck where he worked as a tailor and entered the fur trade. Arriving after the initial trading boom, he enjoyed the success that often rewarded hard working newcomers.

In 1664, he purchased a lot in Albany and later set up his home on the south side of upper State Street. Hendrick prospered in Albany and was able to obtain Schenectady property, a patent in the Mohawk Valley, and also build a new house in New York City. In 1676, he purchased a small boat. In 1685, he was commissioned a lieutenant in the Albany County militia. He was named first ward alderman in 1686 and 1687. He also served as assessor and justice. An all-around community leader, he was a member and officer of the Albany Dutch church.

He may have moved back to Manhattan during the late 1680s where he became a supporter of the insurgant Jacob Leisler.

Hendrick Cuyler filed a will in March 1690. It provided for his eight living children but left the entire estate to his wife Anna during her widowhood. The will passed probate later that Spring!